Hydrochloric Acid → {[(2R)-1-(benzyloxy)hex-4-en-2-yl]oxy}acetaldehyde
Reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C@H:7]([CH2:17][CH:18]=[CH:19][CH3:20])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.Cl>O1CCCC1>[CH2:10]([O:9][CH2:8][C@H:7]([O:6][CH2:5][CH:4]=[O:3])[CH2:17][CH:18]=[CH:19][CH3:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of ({[(2R)-2-(2,2-diethoxyethoxy)hex-4-en-1-yl]oxy}methyl)benzene (C10) (350 g from the previous step, ≦0.64 mol) in tetrahydrofuran (1.4 L) was added aqueous hydrochloric acid (2 M, 700 mL), and the reaction mixture was stirred at 75° C. for 1 hour. Solvent was removed in vacuo and the aqueous residue was extracted with ethyl acetate (2.0 L). The combined organic layers were washed with saturated aqueous sodium chloride solution (3×500 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was obtained as a pale brown oil (210 g, ≦0.64 mol), which was taken directly to the following step.
Workup
- customSolvent was removed in vacuo
- extractionthe aqueous residue was extracted with ethyl acetate (2.0 L)
- washThe combined organic layers were washed with saturated aqueous sodium chloride solution (3×500 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-427ed8f5c52f4ebfbcc3189b453f70a4
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260455B2
Reaction notes
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